Pouzar V, Cerný I
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague.
Steroids. 1996 Feb;61(2):89-93. doi: 10.1016/0039-128x(95)00198-y.
Mixtures of 3E and 3Z isomers of 3-(O-(2-carboxyethyl)oxime (CEO) derivatives of testosterone and 17 alpha-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers were separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosterone and 17 alpha-methyltestosterone. By the same method, after oximation, methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave (3E,2OR)-20-hydroxypregn-4-en-3-one 3(O-(2-carboxyethyl)oxime and (3Z,20R)-20-hydroxypregn-4-en-3-one 3-(O-(2-carboxyethyl))oxime methyl esters. The oxidation and subsequent hydrolysis of these compounds produced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E/Z-isomers of 3-CEO derivatives are designed for the development of immunoanalytical systems, which make use of the bridge heterology based on the geometric isomerism.
通过与（O-(2-羧乙基)）羟胺反应制备了睾酮和17α-甲基睾酮的3-(O-(2-羧乙基)肟（CEO）衍生物的3E和3Z异构体混合物。这些异构体在转化为甲酯后进行分离，温和的碱性水解回收了睾酮和17α-甲基睾酮的3-CEO衍生物的纯E/Z异构体。通过相同的方法，在肟化、甲基化和分离后，（20R）-20-羟基孕-4-烯-3-酮得到了（3E,20R）-20-羟基孕-4-烯-3-酮3-(O-(2-羧乙基)肟和（3Z,20R）-20-羟基孕-4-烯-3-酮3-(O-(2-羧乙基))肟甲酯。这些化合物的氧化及随后的水解产生了孕酮的3-CEO衍生物的3E和3Z异构体。3-CEO衍生物的纯E/Z异构体被设计用于开发免疫分析系统，该系统利用基于几何异构的桥异质性。
